Mark Redman (5-15, 4.98) vs. Mark Mulder (15-7, 3.54). Mulder's last win came August 22 against the Pirates. It's possible I'm mistaken, but I believe Redman's last win came in 1898 against the punchless St. Louis Browns. I mean, true, players then had never heard of steroids, weighed about 112 pounds, rode trains to games, and had to work second jobs during the offseason - and in a league where all teams faced these obstacles, the Browns only managed to win 39 of their 150 games. But man, you should have seen Redman that day.
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